Triethylamine → HCID 21022372, compound

HRID 1794607Notes

Reaction equation

HRID 1794607 reaction equation
[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]([C:15]1[N:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:17](=[O:25])[C:18]2[C:23]([CH3:24])=[N:22][S:21][C:19]=2[N:20]=1)[CH2:13][CH3:14])([CH3:4])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:33])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH:12]([C:15]1[N:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:17](=[O:25])[C:18]2[C:23]([CH3:24])=[N:22][S:21][C:19]=2[N:20]=1)[CH2:13][CH3:14])[C:39](=[O:40])[C:38]1[CH:42]=[CH:43][C:35]([Cl:34])=[CH:36][CH:37]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 21022371HCID 21022371, compound

Product 1

HCID 21022372HCID 21022372, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of 33 (350 mg, 0.74 mmol), 4-chlorobenzoyl chloride (390 mg, 2.29 mmol) and Et3N (412 μl, 2.96 mmol) in CH2Cl2 was stirred at room temperature for 14 h. The mixture was purified by silica gel column directly to give 34 (301 mg, 67%). 34 had an analytical HPLC retention time=4.41 min. (Column: YMC S5 Combiscreen 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4).

Workup

  1. customThe mixture was purified by silica gel column directly

Sources & evidence

ORD record
ord-4dd506b45a824c0788386444a59c7e5e
Source dataset
uspto-grants-2006_04
Patent number
US07022850B2

Reaction notes

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